Abstract
An efficient synthesis of novel type of dipyrido-1,4-thiazine (4) was elaborated in the reactions of two pairs of 3,4-disubstituted pyridines in DMF. The reactions proceeded through the S→N type of the Smiles rearrangement of the resulting 4,4'-dipyridinyl sulfide. In the case of formation of 10-(3'-nitro-4'- pyridinyl)-2,7-diazaphenothiazine (5) double rearrangement was observed. 10H- 2,7-diazaphenothiazine (4) was N-alkylated, N-arylated and N-heteroarylated to give 10-substituted (alkyl, arylalkyl, aryl, heteroaryl and dialkylaminoalkyl) derivatives (5) and (17-29). The NMR spectra were assigned with the help of the 1 H- 1 H correlation (COSY) and NOE experiment of the methyl derivative (17). The crucial 10H-2,7-diazaphenothiazine (4) showed promising anticancer activity.
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